Collective Synthesis of Phenanthridinone through C-H Activation Involving a Pd-Catalyzed Aryne Multicomponent Reaction

Minghao Feng; Bingqing Tang; Hong Xi Xu; Xuefeng Jiang

doi:10.1021/acs.orglett.6b02109

Collective Synthesis of Phenanthridinone through C-H Activation Involving a Pd-Catalyzed Aryne Multicomponent Reaction

Minghao Feng
, Bingqing Tang
, Hong Xi Xu
, Xuefeng Jiang^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

Research output: Contribution to journal › Article › peer-review

68 Scopus citations

Abstract

A palladium-catalyzed multicomponent reaction (MCR) involving aryne, CO, and aniline is established for straightforward assembly of a phenanthridinone scaffold through C-H bond activation. Free combination with multiple kinds of readily available anilines and arynes is facilely achieved for phenanthridinone construction without prefunctionalization. Representative natural products were subsequently synthesized through this MCR strategy highly efficiently. Control experiments and interval NMR tracking revealed the mechanism, particularly the key role of CuF₂ in determining the aryne-releasing rate from the precursor in this transformation.

Original language	English
Pages (from-to)	4352-4355
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	17
DOIs	https://doi.org/10.1021/acs.orglett.6b02109
State	Published - 2 Sep 2016

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title = "Collective Synthesis of Phenanthridinone through C-H Activation Involving a Pd-Catalyzed Aryne Multicomponent Reaction",

abstract = "A palladium-catalyzed multicomponent reaction (MCR) involving aryne, CO, and aniline is established for straightforward assembly of a phenanthridinone scaffold through C-H bond activation. Free combination with multiple kinds of readily available anilines and arynes is facilely achieved for phenanthridinone construction without prefunctionalization. Representative natural products were subsequently synthesized through this MCR strategy highly efficiently. Control experiments and interval NMR tracking revealed the mechanism, particularly the key role of CuF2 in determining the aryne-releasing rate from the precursor in this transformation.",

author = "Minghao Feng and Bingqing Tang and Xu, \{Hong Xi\} and Xuefeng Jiang",

note = "Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

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T1 - Collective Synthesis of Phenanthridinone through C-H Activation Involving a Pd-Catalyzed Aryne Multicomponent Reaction

AU - Feng, Minghao

AU - Tang, Bingqing

AU - Xu, Hong Xi

AU - Jiang, Xuefeng

PY - 2016/9/2

Y1 - 2016/9/2

N2 - A palladium-catalyzed multicomponent reaction (MCR) involving aryne, CO, and aniline is established for straightforward assembly of a phenanthridinone scaffold through C-H bond activation. Free combination with multiple kinds of readily available anilines and arynes is facilely achieved for phenanthridinone construction without prefunctionalization. Representative natural products were subsequently synthesized through this MCR strategy highly efficiently. Control experiments and interval NMR tracking revealed the mechanism, particularly the key role of CuF2 in determining the aryne-releasing rate from the precursor in this transformation.

AB - A palladium-catalyzed multicomponent reaction (MCR) involving aryne, CO, and aniline is established for straightforward assembly of a phenanthridinone scaffold through C-H bond activation. Free combination with multiple kinds of readily available anilines and arynes is facilely achieved for phenanthridinone construction without prefunctionalization. Representative natural products were subsequently synthesized through this MCR strategy highly efficiently. Control experiments and interval NMR tracking revealed the mechanism, particularly the key role of CuF2 in determining the aryne-releasing rate from the precursor in this transformation.

UR - https://www.scopus.com/pages/publications/84985945532

U2 - 10.1021/acs.orglett.6b02109

DO - 10.1021/acs.orglett.6b02109

M3 - 文章

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SN - 1523-7060

VL - 18

SP - 4352

EP - 4355

JO - Organic Letters

JF - Organic Letters

IS - 17

ER -

Collective Synthesis of Phenanthridinone through C-H Activation Involving a Pd-Catalyzed Aryne Multicomponent Reaction

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